Advanced Organic Chemistry: Traditional Cross Coupling Reactions

In this installment of the Synthesis Workshop Advanced Organic Chemistry course, Dr. Thomas Verheyen joins us to give us an overview of traditional cross coupling reactions.
This talk also has an associated problem set, which is available at synthesis-workshop.com/#probl....
References in main presentation (in order of appearance):
For reviews on cross coupling see: (a) Metal-catalyzed cross coupling reactions (Wiley) 2013 (ISBN: 9783527331543); (b) Chem. Rev. 2011, 111, 2177; (c) Organometallics 2019, 38, 3.
(a) Ber. Dtsch. Chem. Ges. 1869, 2, 422; (b) Ann. Chem. Pharm. 1870, 154, 137; (c) Ber. Dtsch. Chem. Ges. 1882, 15, 5; (d) Ber. Dtsch. Chem. Ges. 1901, 34, 2174; (e) Chim. Phys. 1855, 44, 275; (f) Ann. Chem. 1862, 121, 361; (g) J. Chem. Soc. Trans. 1914, 105, 1057.
(a) Seances Acad. Sci. 1924, 179, 330; (b) J. Prakt. Chem. 1939, 152, 237; (c) JACS 1941, 63, 2316; (d) JACS 1943, 65, 504; (e) J. Organomet. Chem. 2002, 653, 11; (f) Ann. Chim. Paris 1957, 2, 819; (g) JOC 1963, 28, 3313.
(a) J. Organomet. Chem. 1970, 24, 63; (b) JACS 1971, 93, 5908; (c) J. Chem. Soc., Chem. Commun. 1972, 144; (d) JACS 1972, 94, 9268; (e) JACS 1972, 94, 4374; (f) OPRD 2008, 12, 69 (g) J. Organomet. Chem. 1975, 91, C39.
(a) Angew. Chem. 1959, 71, 176; (b) Chem. Commun. 1968, 6; (c) JACS 1968, 90, 5518; (d) Synlett 2006, 2855 (Heck perspective; (e) Bull. Chem. Soc. Jpn. 1971, 44, 581; (f) JOC 1972, 37, 2320; (g) OPRD 2008, 12, 637; (h) JACS 1996, 118, 10766.
(a) J. Organomet. Chem. 1975, 93, 253; (b) J. Organomet. Chem. 1975, 93, 259; (c) Tetrahedron Lett. 1975, 16, 4467; (d) Angew. Chem. 2001, 113, 623.
(a) J. Chem. Soc. Chem. Commun. 1976, 596b; (b) JOC 1977, 42, 1821; (c) Acc. Chem. Res. 1982, 15, 340 (Negishi perspective); (d) JOC 2003, 68, 3238; (f) ACIE 2006, 45, 6040.
(a) J. Organomet. Chem. 1977, 129, C36; (b) JACS 1978, 100, 3636; (c) J. Organomet. Chem. 1983, 250, 551; (d) JOC 1979, 44, 2408; (e) Nat. Chem. 2013, 5, 667; (f) JOC 1988, 53, 918; (g) JACS 2009, 131, 3104; (h) JACS 1998, 120, 4123.
(a) J. Chem. Soc., Chem. Commun. 1979, 866; (b) Chem. Rev. 1995, 95, 2457 (review by Miyaura and Suzuki); (c) Chem. Eur. J. 2011, 17, 2492 (role of the base); (d) J. Med. Chem. 2016, 59, 10, 4443; (e) JACS 1987, 109, 4756.
(a) Tetrahedron Lett. 1998, 39, 3189; (b) JACS 2000, 122, 11260; (c) Asian J. Org. Chem. 2018, 7, 490 (review Srogl-coupling).
(a) JOC 1995, 60, 7508; (b) Tetrahedron Lett. 1997, 38, 3841; (c) JOC 2012, 77, 8678.
(a) Chem. Lett. 1978, 7, 13; (b) Chem. Lett. 1983, 12, 927; (c) ACIE 1995, 34, 1348; (d) Tetrahedron Lett. 1995, 36, 3609; (e) ACIE 2006, 45, 4321; (f) Tetrahedron Lett. 1998, 39, 2933; (g) Tetrahedron Lett. 1998, 39, 2941; (h) Tetrahedron Lett. 1998, 39, 2937.
(a) Acc. Chem. Res. 2008, 41, 1534; (b) Angew. Chem. Int. Ed. 2019, 58, 17118; (c) Acc. Chem. Res. 2008, 41, 1523.
(a) JOC 1982, 47, 4161; (b) Chem. Soc. Rev. 2011, 40, 4963; (c) Chem. Sci. 2017, 8, 6525; (d) Chem. Sci. 2019, 10, 9865; (e) Chem. Rev. 2006, 106, 4622; (f) JACS 2019, 141, 13346; (g) Chem. Soc. Rev. 2013, 42, 5270; (h) ACIE 2018, 57, 12573.
(a) Chem. Soc. Rev. 2014, 43, 412; (b) JOC 2015, 80, 7837; (c) Aldrichimica Acta. 2009, 42, 17; (d) Org. Lett. 2010, 12, 4384 (e) J. Am. Chem. Soc. 2008, 130, 466.
(a) Chem. Soc. Rev. 2011, 40, 4986; (b) ACIE 2009, 48, 4114; (c) Chem. Soc. Rev. 2018, 47, 172; (d) Chem. Rev. 2019, 119, 2090; (e) Chem. 2019, 5, 526; (f) React. Chem. Eng. 2020, 5, 615 (ex situ gas); (g) Acc. Chem. Res. 2016, 49, 594 (ex situ gas).
For additional references, see final slide.
Graphic on the popularity of the Suzuki-Miyaura coupling in medicinal chemistry - source: J. Med. Chem. 2016, 59, 10, 4443-4458 (doi.org/10.1021/acs.jmedchem.... this is an unofficial adaptation of an article that appeared in an ACS publication. ACS has not endorsed the content of this adaptation or the context of its use.

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